I have had anal sex manyy times and i would suggest that you try it missionary style with your legs up on his shoulders. If you are lubed up it really shouldn't hurt much, sometimes the intital penetration hurts but if you just get through that first
pain it should be fine. It also depends on the time you try it, one day it could be painless and another time it coudl hurt a bit, it definitely depends on your body. Make sure you go to the bathroom, or at least try, beforehand, so you can be comfortable.
hope that helped
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